DeRozan attended Compton High School and was ranked as one of the top college recruits in the nation from the class of 2008. He was ranked #3 in the nation by Rivals.com and #6 by Scout.com.[1]

He played on the varsity basketball team for all four years of high school. As a freshman, he averaged 26.1 points and 8.4 rebounds. During his sophomore year, he averaged 22.6 points and 8.4 rebounds, while as a junior he averaged 22.3 points, 7.8 rebounds, 3.0 assists, and 3.2 steals.[2]

As a senior averaging 29.2 ppg and 7.9 rpg,[3] DeRozan led Compton High School to a 26-6 record, a second consecutive Moore League championship and the CIF Division IAA Southern Section quarter-finals. For his efforts he was awarded the Moore League Most Valuable Player Award and named to the California All-State team. DeRozan was a member of the 2008 McDonald's All-American Team, and also won the 2008 McDonald's All-American Slam Dunk Competition.[4] He was also invited to play in the 2008 Jordan Brand Classic at Madison Square Garden and the Nike Hoop Summit, where he scored a team-high 17 points.[5] DeRozan's achievements on the court in his senior year saw him earn first-team Parade All-American honors and First Team Best in the West honors.

In his first game for the Trojans, DeRozan scored a team-high 21 points with seven rebounds in an exhibition game against Azusa Pacific, an 85–64 victory at the Galen Center.[7] DeRozan had 14 points in his first career regular season game in a win over UC Irvine.[8] He scored 21 points along with a career-high 13 rebounds against UCLA in the Pac-10 Tournament semifinals, before scoring a career-high 22 points on 10-for-16 shooting to lead his team to a 61-49 win over Arizona State in the Pac-10 Tournament final.[9] His efforts in the tournament saw him earn First Team Pac-10 All-Freshman honors in addition to being named Pac-10 Tournament MVP. They went to the 2009 NCAA Men's Division I Basketball Tournament as a 10th seed, where they lost in the 2nd round to Michigan State.

DeRozan started all 35 season games for the Trojans, scoring in double figures 28 times and posting four double-doubles. He ranked third on team in points (13.9 ppg), second in rebounds (5.7 rpg), third in assists (1.5 apg), and second in field-goal percentage (.523, eighth-best in conference). DeRozan followed his regular-season efforts by averaging 19.8 points in USC's five postseason games. His 485 points ranks third all-time and his 201 rebounds is fourth all-time for a USC freshman.[2]

On April 8, 2009, DeRozan announced his decision to enter the 2009 NBA draft and forgo his final three years of eligibility at USC.[10] On June 25, 2009, he was selected ninth overall by the Toronto Raptors in the 2009 draft.[11] He stated that part of the reason he left for the NBA after only one year at USC was to help take better care of his mother, who suffers from lupus.[11]

On July 9, 2009, DeRozan signed his rookie scale contract with the Raptors.[12] As the fourth contestant in the 2010 Sprite Slam Dunk Competition, DeRozan lost in the final round against three-time champion Nate Robinson. The final percentage was 51% to 49%. DeRozan was selected to compete for the 2011 Sprite Slam Dunk Competition as a replacement for injured guard Brandon Jennings. He finished in third place.

On December 31, 2010, DeRozan scored a then career-high 37 points against the Houston Rockets. He matched that career-high two more times against the Utah Jazz on November 12, 2012 and against the Chicago Bulls on November 15, 2013.

On January 22, 2014, DeRozan scored a then career-high 40 points against the Dallas Mavericks, shooting 15-of-22 from the field. On January 30, DeRozan was selected for the 2014 NBA All-Star Game as a reserve guard for the Eastern Conference All-Star team. He finished the game with 8 points, 3 rebounds and 2 assists in 15 minutes. On February 1, he recorded a 36 points and a career-high 12 assists in a loss to the Portland Trail Blazers. On March 28, he led the Raptors to a playoff berth for the first time since 2008, with a victory over the Boston Celtics. He scored 30 points in the win, along with 3 rebounds, 4 assists and 1 steal. On April 13, he scored 30 points against the Detroit Pistons to lead the Raptors to tie a franchise record of 47 wins.

DeRozan's 2013–14 season was a breakout year, averaging career-highs of 22.7 points, 4.3 rebounds, 4.0 assists, 30% from beyond the arc, and finished fourth in total free-throws made and seventh in attempts. He led the Raptors to a 48–34 record and a third-seed finish in the Eastern Conference.

In DeRozan's first playoff game against the Brooklyn Nets on April 19, 2014, DeRozan scored 14 points on a 3-of-13 shooting as the game resulted in a loss. In Game 2, DeRozan bounced back and scored 30 points on 9-of-21 shooting in a 100–95 win. On April 25, he recorded 30 points, 5 rebounds, and 5 assists in a loss. That 30-point game made DeRozan the first Raptor to score 30 points in back-to-back playoffs games, and the first Raptor to score 30 in multiple playoff games since Vince Carter. The Raptors went on to lose to the Nets in seven games.

In the Raptors' season opening game of the 2014–15 season against the Atlanta Hawks in Toronto, DeRozan recorded career-highs with 11 rebounds and six steals, along with 15 points, in a 109–102 win.[13] On November 29, 2014, he was ruled out indefinitely with a torn left adductor longus tendon. He sustained the injury the night before at the 8:23 mark of the third quarter against the Dallas Mavericks and did not return.[14] On January 14, 2015, he returned to action, scoring 20 points on 9-of-14 shooting in a 100–84 win over the Philadelphia 76ers.[15] On March 2, he scored a season-high 35 points in a 114–103 win over the Philadelphia 76ers.[16] On March 30, DeRozan scored a career-high 42 points in a 99–96 win over the Houston Rockets.[17] On April 17, he was named Eastern Conference Player of the Month for April, joining Kyle Lowry (December 2014) and Chris Bosh (January 2007) as the only players in team history to be named Player of the Month.[18]

On April 24, in Game 3 of the Raptors' first-round playoff series with the Washington Wizards, DeRozan scored a playoff career-high 32 points while scoring a franchise playoff-record 20 points in the first quarter, surpassing Vince Carter's previous record of 19 points in a first quarter of a playoff game.[19]

On November 10, 2015, DeRozan scored a then season-high 29 points in a loss to the New York Knicks. Reaching the 15-point mark for the eighth straight game to start the season, he became the first Raptor since Chris Bosh in 2009–10 to accomplish the feat.[20] On December 14, DeRozan was named Eastern Conference Player of the Week for games played December 7–13, earning the honor for the first time in his seven-year career and became the seventh player in team history to be named Player of the Week.[21] On January 8, he scored a then season-high 35 points in a 97–88 win over the Washington Wizards.[22] On January 28, he was named an Eastern Conference All-Star reserve for the 2016 NBA All-Star Game, earning his second All-Star nod in three years.[23][24] On February 2, DeRozan and teammate Kyle Lowry were selected as co-winners for Eastern Conference Player of the Month for January. The pair helped the Raptors go 12–2 during the month and recorded a franchise-record 11-game win streak.[25] On February 22, he became the winningest player in Raptors history, passing Chris Bosh and Morris Peterson with his 233rd career win. With 22 points, he helped the Raptors defeat the New York Knicks 122–95.[26] On March 4, he scored a season-high 38 points in a 117–115 win over the Portland Trail Blazers. In that game, he set an NBA record with 24 consecutive free throws made in one game.[27] On March 12, he tied his season-high of 38 points while also recording 10 rebounds and seven assists in a 112–104 overtime win over the Miami Heat.[28] On March 30, he scored 26 points in a 105–97 win over the Atlanta Hawks, helping the Raptors record a 50-win season for the first time in franchise history.[29] On April 10, he scored 27 points in a 93–89 win over the New York Knicks in New York, setting a franchise record with 23 road victories in a season. DeRozan also moved ahead of Vince Carter for second on the Raptors' career scoring list, trailing only Chris Bosh.[30]

The Raptors finished the regular season as the second seed in the Eastern Conference with a 56–26 record. In the first round of the playoffs, the Raptors faced the seventh-seeded Indiana Pacers, and in a Game 5 win on April 26, DeRozan scored 34 points to help the Raptors take a 3–2 series lead.[31] In Game 7 of the series, DeRozan scored 30 points to help the Raptors win a best-of-seven series for the first time in franchise history. With a 4–3 series victory over the Pacers, the Raptors moved on to the second round to face the Miami Heat.[32] In Game 5 of the Raptors' series with the Heat, DeRozan again scored 34 points to help the Raptors take a 3–2 series lead with a 99–91 win.[33] In Game 7 of the series, he scored 28 points in a 116–89 win over the Heat, helping the Raptors advance to the conference finals for the first time in franchise history.[34] In Game 4 of the Eastern Conference Finals against the Cleveland Cavaliers, DeRozan scored 32 points to help the Raptors win 105–99 and tie the series at 2–2.[35] The Raptors went on to lose the next two games to bow out of the playoffs with a 4–2 defeat.

On July 14, 2016, DeRozan re-signed with the Raptors to a five-year, $139 million contract.[36][37] In the Raptors' season opener on October 26, 2016, DeRozan had his third career 40-point outing in a 109–91 win over the Detroit Pistons.[38] Two days later, he had a 32-point effort in a 94–91 loss to the Cleveland Cavaliers. DeRozan's combined 72 points bested Vince Carter's team record of 65 for the most points through the first two games of a season, set in the 2003–04 season.[39] With a 33-point effort on October 31 against the Denver Nuggets, DeRozan became the first ever Raptor with three straight 30-point games to begin a season.[40] With 40 points against the Washington Wizards on November 2, DeRozan tied Mike James' franchise record with four consecutive 30-point games.[41] He passed that mark two days later, scoring 34 points in a 96–87 win over the Miami Heat. His five straight 30-point games set the best such start to a season since Michael Jordan did it for six straight games to open the 1986–87 season.[42] On November 12, he scored 33 points against the New York Knicks for his eighth 30-point game in nine games, becoming only the fourth player to register 30-plus points in eight of the first nine games of a season, joining Michael Jordan, World B. Free and Tiny Archibald.[43] DeRozan was subsequently named Eastern Conference Player of the Week for games played Monday, November 7 through Sunday, November 13.[44] With 34 points against the Golden State Warriors on November 16, DeRozan became the first NBA player with nine 30-point games in his team's first 11 games since Jordan in 1987–88.[45] DeRozan's six field goals against the Los Angeles Lakers on December 2 saw him pass Vince Carter (3,536) for second on the franchise's all-time list; Chris Bosh leads the way with 3,614.[46]